diff --git a/test/api/v3/unit/libs/payments.test.js b/test/api/v3/unit/libs/payments.test.js
index 058f312125..17b6870db0 100644
--- a/test/api/v3/unit/libs/payments.test.js
+++ b/test/api/v3/unit/libs/payments.test.js
@@ -153,6 +153,24 @@ describe('payments/index', () => {
         expect(recipient.purchased.plan.dateUpdated).to.exist;
       });
 
+      it('sets plan.dateUpdated if it did exist but the user has cancelled', async () => {
+        recipient.purchased.plan.dateUpdated = moment().subtract(1, 'days').toDate();
+        recipient.purchased.plan.dateTerminated = moment().subtract(1, 'days').toDate();
+        recipient.purchased.plan.customerId = 'testing';
+
+        await api.createSubscription(data);
+
+        expect(moment(recipient.purchased.plan.dateUpdated).date()).to.eql(moment().date());
+      });
+
+      it('sets plan.dateUpdated if it did exist but the user has a corrupt plan', async () => {
+        recipient.purchased.plan.dateUpdated = moment().subtract(1, 'days').toDate();
+
+        await api.createSubscription(data);
+
+        expect(moment(recipient.purchased.plan.dateUpdated).date()).to.eql(moment().date());
+      });
+
       it('sets plan.dateCreated if it did not previously exist', async () => {
         expect(recipient.purchased.plan.dateCreated).to.not.exist;
 
diff --git a/website/server/libs/payments.js b/website/server/libs/payments.js
index 5d453a172f..9b9882ae2c 100644
--- a/website/server/libs/payments.js
+++ b/website/server/libs/payments.js
@@ -307,7 +307,7 @@ api.createSubscription = async function createSubscription (data) {
     if (plan.customerId && !plan.dateTerminated) { // User has active plan
       plan.extraMonths += months;
     } else {
-      if (!plan.dateUpdated) plan.dateUpdated = today;
+      if (!recipient.isSubscribed() || !plan.dateUpdated) plan.dateUpdated = today;
       if (moment(plan.dateTerminated).isAfter()) {
         plan.dateTerminated = moment(plan.dateTerminated).add({months}).toDate();
       } else {
diff --git a/website/server/models/user/methods.js b/website/server/models/user/methods.js
index 909f57d83f..f752dc165f 100644
--- a/website/server/models/user/methods.js
+++ b/website/server/models/user/methods.js
@@ -19,9 +19,8 @@ import paypalPayments from '../../libs/paypalPayments';
 const daysSince = common.daysSince;
 
 schema.methods.isSubscribed = function isSubscribed () {
-  let now = new Date();
-  let plan = this.purchased.plan;
-
+  const now = new Date();
+  const plan = this.purchased.plan;
   return plan && plan.customerId && (!plan.dateTerminated || moment(plan.dateTerminated).isAfter(now));
 };